Water → HCID 18444650, compound

HRID 2266827Notes

Reaction equation

HRID 2266827 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH3:19])=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[CH:13]=2)[CH:9]=1)=[O:4].[OH-].[Li+].O>O1CCCC1>[I:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][CH2:10][C:8]1[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[O:6][C:7]=1[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58824154HCID 58824154, compound

Product 1

HCID 18444650HCID 18444650, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(3-iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (106) (2.7 g, 7.25 mmoles) and lithium hydroxide (1.5 g, 36.25 mmoles) in tetrahydrofuran (25 ml) containing water (2 ml) was stirred at room temperature for 3 h. The tetrahydrofuran was evaporated, the residue was diluted with water and the mixture acidified to pH=1 with 1M aqueous hydrochloric acid. The precipitate was collected washed with water and dried at 70° C. in vacuo to give compound 107 (1.76 g) as a white solid. LC/MS System B; Rt=3.51 mins, m/z (ES−)=357 (M−H for C13H11IO4).

Workup

  1. customThe tetrahydrofuran was evaporated
  2. additionthe residue was diluted with water
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried at 70° C. in vacuo

Sources & evidence

ORD record
ord-faeea7a9ebb84da39736f7e77a233d62
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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